Software Lead Weekly
Issue #672, 10th October 2025
This Week's Favorite
44 Harsh Truths About Money, Status, and Human Nature - Naval Ravikant (Video)
196 minutes read.
Naval Ravikant in a long-form interview? If you know me well enough, you know this is the best combo for me. Naval shares his philosophical (and highly practical) takes on many areas in life that I believe you'll enjoy (and get a lot from!) on your next commute to work.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
196 minutes read.
Naval Ravikant in a long-form interview? If you know me well enough, you know this is the best combo for me. Naval shares his philosophical (and highly practical) takes on many areas in life that I believe you'll enjoy (and get a lot from!) on your next commute to work.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Culture
This Is How HR and Finance Guys Arrive to Tell You That There Is No Bonus This Year
1 minutes read.
My humble effort to help you start the weekend with a smile on your face.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
1 minutes read.
My humble effort to help you start the weekend with a smile on your face.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Why Operators Are Paying Attention to the Rise of GTM Engineers, and What They Actually Do
4 minutes read.
"If you crack it, your SDRs become dramatically more productive. They can focus on actual connection, while the system handles the grunt work." -- Bobby Pinero is spot on that as long as humans buy from humans, we should automate the grunt work and let humans focus on how to build the right relationships. GTM organization will need to build a robust operation system to operate effectively and efficiently at scale. Make sure you hire the right engineers who know how to do that (the robust operation side) rather than only stitching together a few solutions.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
4 minutes read.
"If you crack it, your SDRs become dramatically more productive. They can focus on actual connection, while the system handles the grunt work." -- Bobby Pinero is spot on that as long as humans buy from humans, we should automate the grunt work and let humans focus on how to build the right relationships. GTM organization will need to build a robust operation system to operate effectively and efficiently at scale. Make sure you hire the right engineers who know how to do that (the robust operation side) rather than only stitching together a few solutions.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Shirokuro, a Japanese Restaurant in NYC's East Village, Where the Interior Mimics a Hand-Drawn Black-and-White Sketchbook
2 minutes read.
What a cool concept of a restaurant - a product with a clearly differentiated eating experience. It has everything needed to create virality around it easily. What would you do to increase the number of returning customers once "the black & white restraunat" effect is no longer exciting?
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
2 minutes read.
What a cool concept of a restaurant - a product with a clearly differentiated eating experience. It has everything needed to create virality around it easily. What would you do to increase the number of returning customers once "the black & white restraunat" effect is no longer exciting?
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
From Books to Prompts: The Instant Future of Productivity
3 minutes read.
The dance between reading and experimenting is getting easier with AI tools and coding agents. Many of us like to learn by trying out a few small projects. I wonder, though, if AI is writing the artifacts for me, how much am I learning from it? How do we mimic enough failures to understand how things work? "The self-help aisle promised transformation through commitment. AI promises transformation through experimentation." I disagree with Tomasz Tunguz - we often get shortcuts, not transformation. Still, maybe the right mix here can lead to such a transformation. The jury is still out.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
3 minutes read.
The dance between reading and experimenting is getting easier with AI tools and coding agents. Many of us like to learn by trying out a few small projects. I wonder, though, if AI is writing the artifacts for me, how much am I learning from it? How do we mimic enough failures to understand how things work? "The self-help aisle promised transformation through commitment. AI promises transformation through experimentation." I disagree with Tomasz Tunguz - we often get shortcuts, not transformation. Still, maybe the right mix here can lead to such a transformation. The jury is still out.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Peopleware
Face It: You're a Crazy Person
9 minutes read.
Unpacking the role or career you're considering is an interesting way to eliminate options. I wonder if it's truly possible to know the answer before you try it out enough to understand how it makes you feel: "What should I do with my life?” is really a post-1850 problem, which means, in the big scheme of things, we haven’t had any time to work on it. The beginning of that work is, I believe, unpacking. As you slice open the boxes and dump out the components of your possible futures, I hope you find the job that’s crazy in the same way that you are crazy."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
9 minutes read.
Unpacking the role or career you're considering is an interesting way to eliminate options. I wonder if it's truly possible to know the answer before you try it out enough to understand how it makes you feel: "What should I do with my life?” is really a post-1850 problem, which means, in the big scheme of things, we haven’t had any time to work on it. The beginning of that work is, I believe, unpacking. As you slice open the boxes and dump out the components of your possible futures, I hope you find the job that’s crazy in the same way that you are crazy."
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
On Walking Away From Success, Wandering With Purpose, and the Things Worth Not Scaling
7 minutes read.
"When you’ve proven you can win the game, the real question becomes: Is this the game you want to keep playing? [...] In tech, “doesn’t scale” is a death sentence. In life, it’s the highest praise. Unscalable things resist corruption by external rewards. They remain yours. Pure. Authentic. [...] After decades learning to scale everything, I’m learning to think smaller. To do things that only work one-on-one. To find satisfaction in repetition, in daily practice, in the ritual itself rather than results." -- Yew Jin Lim shares an honest and intimate journey, sharing his fears and joy in different kinds of discoveries. In a life of privilege working in a high-paid industry, we often seek a global maximum, as if there is one. We feel safe enough to explore. There is no recipe for living a worthy life, so don't read it to copy it, but rather to gain a perspective on one option.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
7 minutes read.
"When you’ve proven you can win the game, the real question becomes: Is this the game you want to keep playing? [...] In tech, “doesn’t scale” is a death sentence. In life, it’s the highest praise. Unscalable things resist corruption by external rewards. They remain yours. Pure. Authentic. [...] After decades learning to scale everything, I’m learning to think smaller. To do things that only work one-on-one. To find satisfaction in repetition, in daily practice, in the ritual itself rather than results." -- Yew Jin Lim shares an honest and intimate journey, sharing his fears and joy in different kinds of discoveries. In a life of privilege working in a high-paid industry, we often seek a global maximum, as if there is one. We feel safe enough to explore. There is no recipe for living a worthy life, so don't read it to copy it, but rather to gain a perspective on one option.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Review: Working Backwards by Colin Bryar and Bill Carr
8 minutes read.
"To minimize the Bar Raiser’s bias, the Bar Raiser can never be the hiring manager, and is typically someone completely outside the immediate team doing the hiring. Moreover, the Bar Raiser is never punished because a role went unfilled for a longer period of time." -- The last part is the key one. The Bar Raiser cares only about quality without any other (wrong) incentive. This book review from Yevgeniy Brikman is packed with many gems you can take as is, or hopefully invest more time to read the book and the stories behind it. It's a good book, so I recommend it to every engineering manager who seeks to level up their organization.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
8 minutes read.
"To minimize the Bar Raiser’s bias, the Bar Raiser can never be the hiring manager, and is typically someone completely outside the immediate team doing the hiring. Moreover, the Bar Raiser is never punished because a role went unfilled for a longer period of time." -- The last part is the key one. The Bar Raiser cares only about quality without any other (wrong) incentive. This book review from Yevgeniy Brikman is packed with many gems you can take as is, or hopefully invest more time to read the book and the stories behind it. It's a good book, so I recommend it to every engineering manager who seeks to level up their organization.
Read it later via Pocket or Instapaper.
Share it via Twitter or email.
Inspiring Tweets
@alexisohanian: Some days you move a mountain. Some days you move a pebble. Both count. Keep moving.
- Oren
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.
P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.